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Stereoselective Synthesis of Tetrahydrofurans via the Palladium-Catalyzed Reaction of Aryl Bromides with γ-Hydroxy Alkenes: Evidence for an Unusual Intramolecular Olefin Insertion into a Pd(Ar)(OR) Intermediate

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John P. Wolfe* and Michael A. Rossi

Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109-1055

J. Am. Chem. Soc., 2004, 126 (6), pp 1620–1621

DOI: 10.1021/ja0394838

Publication Date (Web): January 23, 2004

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, jpwolfe@umich.edu

Abstract

A new, stereoselective method for the synthesis of substituted tetrahydrofurans from γ-hydroxy alkenes that forms both a C−C and a C−O bond with diastereoselectivities of up to >20:1 is described. Initial mechanistic studies that suggest the reactions proceed via the intramolecular insertion of an olefin into a Pd(Ar)(OR) intermediate are discussed.

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Published In Issue February 18, 2004
Received November 7, 2003

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Communication

Stereoselective Synthesis of Tetrahydrofurans via the Palladium-Catalyzed Reaction of Aryl Bromides with γ-Hydroxy Alkenes: Evidence for an Unusual Intramolecular Olefin Insertion into a Pd(Ar)(OR) Intermediate

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Palladium-Catalyzed Synthesis of N-Aryl-2-benzylindolines via Tandem Arylation of 2-Allylaniline: Control of Selectivity through in Situ Catalyst Modification

Palladium-Catalyzed Synthesis of 2,1‘-Disubstituted Tetrahydrofurans from γ-Hydroxy Internal Alkenes. Evidence for Alkene Insertion into a Pd−O Bond and Stereochemical Scrambling via β-Hydride Elimination

Intramolecular Pd-Catalyzed Carboetherification and Carboamination. Influence of Catalyst Structure on Reaction Mechanism and Product Stereochemistry Intramolecular Pd-Catalyzed Carboetherification and Carboamination. Influence of Catalyst Structure on Reaction Mechanism and Product Stereochemistry

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